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My husband wants to crossdress, and I want to help!

This is my first post, and I'm hoping you wonderful folks can help.

My husband and I have been together for 8 years, married for 2. About three years ago, he and I were having pillow talk and he admitted that one of his fantasies is to wear "fancy clothes," which he told me (after a lot of begging) meant "stockings and stuff." Now, I know that crossdressing is usually not a sexual thing for most men, and I can't say for sure if this is this case with my husband, though he did present it as a sexual fantasy.

I'm asking for help because since mentioning it this once, my husband has been resistant to discussing it further. He's resistant to discuss anything that has to do with sex and sexuality in general, no matter how the subject is presented. I've only mentioned the crossdressing twice since he told me, and both times he said he didn't want to talk about it.

I think this must be something important to him or he wouldn't have mentioned it. He did say he has had this fantasy since he was a young teenager. I don't think he is crossdressing already, since he only mentioned it in the context of sex and is terrible at hiding things from me, but I could be wrong.

My question is, do I purchase some stockings in his size and bring them to bed, despite having never had a conversation with him about living out this fantasy? How do I get him to talk about it? Should I just drop it? I'm new to this and any feedback is appreciated.

Thanks in advance.

Last edited by Nigella; 11-20-2010 at 02:40 PM.
Reason: Removed reference to ?s

Hi and welcome to the site. Most who read your post will say WOW!!! a woman who is open to experimenting with crossdressing he is very lucky to have someone in his life that has an open mind such as yours. Very rare to find someone who is willing in just dressing You could try the old trick of being in bed..and somewhere along the line, tell him how sexy if would be if he put on your stockings or panties.. and then introduce 'his' new items

Some will pull back when confronted with the questions as they are unsure of where it will go..so that is not new. Handle delicately..

Thank you for sharing..

Hugs,Marissa

Last edited by Nigella; 11-20-2010 at 02:45 PM.
Reason: You have been here long enough to know that discussion about sex toys are not permitted on the forum

Marissa

"You better look hard and look twice,...is that me, baby or just a brilliant disguise?"- The Boss

I have a very hard time talking to my wife about it as well, still a lot embarassed about the whole thing while discussing with my wife. I wear womans clothes most days at home and always to bed, we have a modest sex life only because my wife says she is not a lesbian and doesn't want to be with a woman. She humors me though. I would say that he will be reluctant to bring it up again until it really gets bottled up and has to get out, you could buy him a nice nightie and some panties and garter and stockings and have a few drinks and then tell him to go try on the clothes you have laid out for him. , if he is anything like a bunch of us he will love you forever.

Last edited by Nigella; 11-20-2010 at 02:45 PM.
Reason: You have been here long enough to know that discussion about sex toys are not permitted on the forum

my bet is that he is embarrassed about telling you. He has probably done it for most of his life, but wants it to go away. He is ashamed of it. It will take a lot of talking to get to the root issue of this. He is also probably really worried that it will somehow destroy your relationship

i think he is emabarassed to talk to you about the whole thing...i know i sprung the suprise on my wife in august, and we haven't said a word about it since....and for me, at this time, the cross dressing is sexual...i know i get very excited about it..., maybe the cross dressing and everthing is all fantasy...i would sit down and talk to him..the pillow talk is fine..and tell him you support the cross dressing all a guy needs is support from his wife...i know i would love to have that...

I think its also true that that most of us would like to be more submissive in the relationship with GG

At least part if not more than half of the time.

Because of societial, cultural and religious conditioning? I believe many of us "fantazise" about so-called "forced feminization"

Rather focusing on the sexual content it? I would suggest that you work on brining out "the gril" within him out. Letting him express the "her"
that he/she kept bottled up with her/him so long.

Inded I would a suggest using a chaisty device to deny "Her" and outlet and release from his/her "feminity"

This might sound like or suggest some sort of bondage etc ~ but its not ~ its forcing him/her to come to terms with his/her feminiity which he/her has denied themselves for so long ~without any other means?

Everyone is different and we all have different levels of comfort. In my case i can talk to my SO about anything it doesnt matter. But when it comes to the practical application of her seeing me dressed im still a bit on edge about it and the point of me being comfortable in fem clothes around her just hasent come to me yet. But when she is supportive or suggestive its nice. So buying him some stockings and stuff and introducing it to him might be a good idea. He may have to reach his level of comfortableness before he can reach out and address his comfort around you. But if you are supportive it will really help. A couple ways that you can go about it that just kind of pop into my head would be. You can leave the stuff out into the bathroom and tell him theres a surprise in there for him that you want him to wear to bed. You can introduce it while in bed. Or if you could possibly give the things to him as a gift and tell him that you want to see him in it soon or something. You know your husband the best so only you can decide. I hope this helps.

Being dressed up is much better if you have someone else to admire and enjoy it with you.

------------------------------------------------------If I had a world of my own, everything would be nonsense. Nothing would be what it is because everything would be what it isn't. And contrary-wise; what it is it wouldn't be, and what it wouldn't be, it would. You see?
- Alice Kingsley

My advice is to go slow. Introduce one thing at a time, like say panties. You can make a game of it. If he pushes back (like says, no) don't push it. At first, for most CDs, there is a lot of both social and personal hurdles that need to be addressed. You can also do some things that aren't directly related to CDing, but still a bit en femme. Try something asking him to shave his legs or arms (or other areas). Maybe take him to the mall, while there have him follow you into the lingerie department. Find something cute and sexy and tell him this would look good on him. Maybe go to the MAC/Sephora counter and get him some lipstick, masquera and/or eye liner. Matbe go with him to get his ears pierced. But go slow and try to make it seem like a whim, if it seems really planned, he'll likely resist

Many men associate this side of themselves with feelings of submissiveness and vulnerability. That makes it a very delicate thing to approach when dealing with a man who is masculine in all other respects. We're taught that those are bad things to feel. We want to be in control, and to feel emotionally impregnable. There's a lot of fear keeping those defensive walls in place, so you shouldn't try to tear them down by main force. What you want is to be invited inside the walls, and that requires a bond of trust.

If your goal here is to give him an experience that he deeply desires, then you have to ease your way into it. My suggestion is that you should buy the 'fancy clothes' for yourself. Wear them to bed when you make love. Let him experience them vicariously through you. If the two of you are close enough in size, he may try them out when you're not around. Give that some time to simmer, and then tell him some night how much you would love to see how his legs would feel wearing your stockings. Don't present it as a chance for him to fulfill his fantasy, tell him it's yours (as apparently it is). Once he's tried it, you can move on from there. Always be sure to let him go back to being the guy afterwards. Don't be derisive even in a playful way, or you might find yourself shoved outside the wall again.

You're so sweet for coming on this forum to seek advice on how to move forward. I agree with the others who recommend going slow (and that is for both of you). I know when i raised the subject with my wife it felt like my heart was going to jump out of my chest!

In our case it has opened a whole new level to our relationship (both things you mentioned ) and we have had great "fun" together.

Perhaps asking him to wear some panties for the day, with the anticipation of more to come later, will help you both to enjoy it. Or maybe offer to put lipstick on each other, then plant little "lipstick" kisses over each other. Or suggest you both have a steamy shower and shave each other legs. Or ..... holey cow, I need to go see my honey!!

You sound like a wonderful, caring woman. I certainly wish you both the best!

At the start, cross dressing for most men is sexual in orientation, even if they do not admit it to themself. Based upon what you have posted there is little question that his desires are tied to this. The very fact that you are willing to come to this site and ask for assistance says a lot about what a truly great wife you are. In my opinion (and it is only that) I would buy him a sexy nightgown and nylons, leave them out for him to find with a note inviting him to wear them and take you to bed. He will either reject the idea, which says he has a lot of issues to deal with, or accept the offer and you can take things to the next level, if there is one. Again. You are a very special person. Good luck.

A lot of good advice here. I would only add that I think it IS sexual for a lot of us, and at least partly sexual for most of us, though many will deny that. Embarrassment and shame is a powerful force for us. I know that I oscillate between enthusiastic and not about many aspects of my sex life with my wife (including, but not only, the crossdressing).

At the right moment (you'll know when that is), tell him that you love him unconditionally, that you want more than anything for him to be happy, and that the rest is just details. If they fit okay, take a pair of your panties or a sexy nightgown, and help him get into it. I think this is important. He might be too embarrassed to put it on himself, but would love for you to put it on him. After all, he might reason, where is the guilt in cooperating with my wife.

Make sure you tell him that your love is unconditional.
Liz

Sophie86 has some terrific advice a few messages back. Read it twice. Good luck

My suggestion would be to buy him a gift card to a place that sells lingerie. One he can shop online. Let him decide what he would like, or when he is ready. Just be supportive, and let him take his time. This is his fantasy.
To someone who is not fully comfortable with their sexuality, crossdressing can be a very touchy subject. Be careful not to degrade him. Good luck.

I'm hesitant to suggest anything without knowing EXACTLY how you feel about it. All i read from your post is that you are thinking of bringing the items to bed, but you seem to want to do that to get him to open up about it. If you succeed in getting him to wear any items of lingerie to bed only to find out it makes you uncomfortable he will sense that and it will prolly be a very bad situation.
Now if you truly like the idea of having your man in feminine clothing and especially in your bed (there are more GGs who do not allow there CD/TG SOs to dress for bed, or take it into the sexual arena), then by all means take it slowly and carefully in that direction. Make sure to instill in him that you are totally fine with it.

But do you know how you really feel about it, or do you just want to get him to release all this stuff that is bottled up in him? If you are just trying to get it out, i would try to do so just through speaking about it.
I wonder how many SOs out there have said "you want to wear my lingerie?, ok, that sounds like it could be fun" , only to have a very different and awful reaction to seeing their guy dressed.

Be careful what you ask for. Now then if the idea is a turn on for you and you know you can enjoy it, then Hallelujah, best wishes for you both.
mj (Cassie)

Serenity through Femininity

Life isn't about waiting out the storm.....it's about learning to dance in the rain.

Even now, it's tough for me to tell my wife stuff about crossdressing, etc. The best thing you can do, is take the lead on this if you want to help. He's probably scared. Just get the stockings, panties, bra, whatever. Start with one item. Tell him you want him to try it "for you". That'll give him the excuse he needs. You might have to coax him a bit. That's up to you. Good luck!

I really, really appreciate all the feedback I'm getting. It looks like I have a lot to learn.

Something I'm getting from a lot of your posts that surprises me is the assumption that the "stuff" in "stockings and stuff" means things like sexy nightgowns, panties, heels, etc. I guess I didn't automatically assume mentioning one item of clothing meant that he was interested in wearing a LOT of different types of feminine clothing. Do you think this is the case? Did any of you start with a fixation on one type of clothing in particular and expand to others, or do you think an interest in stockings means he wants to fully dress?

Also, very good point, MsMjSerene, about being careful what I ask for. While I am almost certain I wouldn't mind my husband dressing in bed, I can't be 100 percent sure.

I'm also interested in the fact that a lot of you mentioned that dressing IS sexual for you, or at least partly or at first. I also wonder about what some of you have said about your crossdressing being tied to a desire to be submissive.

Please, please, please continue with the feedback. I want to learn as much as I can so I run the smallest risk of hurting my husband or having him lose his trust in me. Thanks again.

I can say that my situation is very similar to yours except that I don't mind talking to my wife about it. In fact, when I first read this thread I thought you might have been her.

No matter. The biggest fear to get over for me was fear of being laughed at or humiliated by her. I dressed fully for the first time last night and she helped me get dressed and even gave me one of her camisoles when she didn't like the top I had on.

Then she kissed me and told me she loves me. That boosted my confidence so much. Do the same for your husband.